Between 1988 and 1991, Cole became popular on TV for playing the part of Jack "Nighthawk" Killian in the series Midnight Caller. In 1999, Cole starred in the film Office Space, in which he portrayed the sadistic office supervisor Bill Lumbergh. When asked about the oft-quoted character, Cole said:

“

"Everyone in Office Space thought that this movie had died. So that's how I knew the movie was actually some kind of success because people were coming up doing some lines from the movie ... It never gets old because it reminds you that something you did had some impact. You could work your whole career and have nothing like that last that long."[5]